1,3-Butadiene → 1-Tris(dimethylamino)silylbut-1-ene

HRID 979692

Reaction equation

HRID 979692 reaction equation
CN([SiH](N(C)C)N(C)C)C.C=CC=C.[CH3:15][N:16]([Si:18]([N:26]([CH3:28])[CH3:27])([N:23]([CH3:25])[CH3:24])[CH:19]=[CH:20][CH:21]=[CH2:22])[CH3:17]>C1(C)C(C)=CC=CC=1>[CH3:15][N:16]([Si:18]([N:26]([CH3:27])[CH3:28])([N:23]([CH3:25])[CH3:24])[CH:19]=[CH:20][CH2:21][CH3:22])[CH3:17]

Participants

5

Reactant 3

HCID 78451,3-ButadieneHCID 84795N,N,N',N',N'',N''-HexamethylsilanetriamineHCID 539962881-Tris(dimethylamino)silylbuta-1,3-diene

Product 1

HCID 536518411-Tris(dimethylamino)silylbut-1-eneYield 32%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
125 °C

Procedure

To a 1 liter autoclave, was added 250 g (1.5 mol) tris(dimethylamino)silane, 100 g xylene, 168 g (3.1 mol) 1,3-butadiene and 200 ppm RhCl(PPh3)3 (0.45 g) as the catalyst. After the autoclave was secured, the reaction was heated to 125° C. for four hours. The reactor was then cooled to room temperature. GC and GC/MS revealed that the major product formed was 1-tris(dimethylamino)silylbuta-1,3-diene in 65% yield. 1-tris(dimethylamino)silylbut-1-ene was also formed in 32% yield.

Workup

  1. temperatureThe reactor was then cooled to room temperature
  2. customformed

Sources & evidence

ORD record
ord-658a7fba799344e9b05c5c355b45109d
Source dataset
uspto-grants-1987_05
Patent number
US04668812

Linked notes

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